Microcapsule with a porous or hollow core and ph-sensitive shell and use thereof

Patent metadata

Field	Value
Publication number	US-12194113-B2
Application number	US-201916967937-A
Country	US
Kind code	B2
Filing date	Feb 1, 2019
Priority date	Feb 6, 2018
Publication date	Jan 14, 2025
Grant date	Jan 14, 2025

Abstract

The invention relates to a microcapsule comprising a hollow or porous core, the hollow or porous core being composed of a polymeric material and containing a component of a redox-initiator system, a shell, the shell being composed of a pH-sensitive material. The microcapsule can be used for formulating dental materials.

First claim

What is claimed is:

1. A curable composition comprising:
polymerizable components bearing a radically-polymerizable unsaturated group; and
a microcapsule comprising:
a hollow or porous core composed of a polymeric material,
a component of a redox-initiator system, the component of a redox-initiator selected for use to initiate curing of the polymerizable components, and
a shell composed of an acid-sensitive material, the acid-sensitive material characterized as being ionic as a result of pH values from 1-4,
wherein the component of a redox-initiator system is encapsulated within the hollow or porous core, and p 2 wherein the shell is at least partly coating the polymeric material.

2. The curable composition of claim 1 , the polymeric material comprising a (meth) acrylate.

3. The curable composition of claim 1 , the porous or hollow core being characterized by the following features alone or in combination:
having a spherical shape;
having a diameter in the range of 1 to 200 μm;
having a pore size from 10 to 200 nm;
being mechanically stable.

4. The curable composition of claim 1 , the shell being characterized by the following features alone or in combination:
thickness: 0.1 to 5 μm;
covering more than 85% of the surface of the porous or hollow core;
soluble in acidic or basic components.

5. The curable composition of claim 1 , the acid-sensitive material being a polymer comprising co-polymer(s) of methyl (meth) acrylate and diethylaminoethyl (meth) acrylate, co-polymer(s) of methyl (meth) acrylate, butyl methacrylate and dimethylaminoethyl (meth) acrylate, or a combination thereof.

6. The curable composition of claim 1 , wherein the component of a redox-initiator system is a reducing agent ascorbic acid comprising an ascorbic acid moiety.

7. The curable composition according to claim 1 , wherein the component of a redox-initiator system is a reducing agent selected from ascorbic acid component(s), tertiary amine component(s), sulfinate component(s), sulphite component(s), borane component(s), (thio)urea component(s), and (thio)barbituric acid component(s), saccharin, and metal salts thereof.

8. The curable composition according to claim 1 , wherein the component of a redox-initiator system is an oxidizing agent selected from hydroperoxide(s), ketone peroxide(s), diacyl peroxide(s), dialkyl peroxide(s), peroxyketal(s), peroxyester(s) and peroxydicarbonate(s), persulfate component(s) and mixtures thereof.

9. The curable composition of claim 1 , being a dental composition or an orthodontic composition.

10. The curable composition of claim 1 , being a dental or orthodontic cement, an adhesive, or a filling material.

11. A process of producing a curable composition of claim 1 , the process comprising the steps of:
providing a hollow or porous core;
providing a component of a redox-initiator system;
allowing the hollow or porous core to absorb the component of the redox-initiator system;
coating the hollow or porous core containing the component of the redox-initiator system therein with an acid-sensitive material to form a microcapsule; and
combining the microcapsule with polymerizable components.

12. The process of claim 11 , the coating step being done by spray-drying at the glass transition temperature T g of the pH-sensitive material.

13. A kit of parts comprising a Catalyst Paste and a Base Paste,
the Catalyst Paste comprising:
a microcapsule comprising:
a hollow or porous core composed of a polymeric material,
a first component of a redox-initiator system, and
a shell composed of an acid-sensitive material, the acid-sensitive material characterized as being ionic as a result of pH values from 1-4,
wherein the first component of a redox-initiator system is encapsulated within the hollow or porous core, and
wherein the shell is at least partly coating the polymeric material; and

the Base Paste comprising:
an acidic component or a basic component,
a second component of a redox-initiator system.

14. The kit of parts according to claim 13 , the Base Paste comprising an acidic component being characterized by the following features alone or in combination:
pKs value: below 5;
comprising an acidic moiety selected from a sulfonic, sulfinic, phosphoric, phosphonic, phosphinic, or carboxylic moiety;
comprising one or more polymerizable moieties.

15. The kit of parts of claim 13 ,
the Catalyst Paste further comprising:
curable non-acidic (meth) acrylate component(s),
filler(s),
optionally photo initiator(s),

the Base Paste B further comprising:
curable (meth) acrylate component(s),
filler(s),
optionally transition metal component(s).

16. A process of curing a curable composition, the process comprising the steps:
providing a kit of parts of claim 15 ,
mixing the Catalyst Past and the Base Paste.

Assignees

• Solventum Intellectual Properties Company

Inventors

• Claussen Kai U
• Mechernich Silke D
• Richter Mareike
• Hecht Reinhold
• Ludsteck Manfred
• Jurjevic Simone

Classifications

• C08F222/10

  Esters · CPC title

• A61C7/00

  Orthodontics, i.e. obtaining or maintaining the desired position of teeth, e.g. by straightening, evening, regulating, separating, or by correcting malocclusions · CPC title

• A61C5/00

  Filling or capping teeth · CPC title

• A61K6/17

  Particle size · CPC title

• A61K6/62

  Photochemical radical initiators · CPC title